Patent GB-956586-A (GB)
Title: Intermediates and polyurethane plastics
IPC: C08G18/56
Filed: 1961-03-01
Abstract: Polyhydroxy compounds suitable for preparing polyurethane resins, are obtained by dissolving a carbohydrate having at least four carbon atoms in a solution of water and an alcohol and/or phenol and an acid catalyst, removing water after reaction of these materials to a residual content of less than one per cent, and reacting the product obtained with a compound containing an alkylene oxide grouping. Aldehydes and ketones may be condensed with the carbohydrate and alcohol or phenol before the water removal step.  Preferably the reaction is effected at 40-100 DEG C. Water is removed by distillation. Pressure may be applied for the reaction and reduced to e.g. 12 mms. Hg/90 DEG C. to complete the removal of the water.  The alkylene oxide is preferably added at 100-200 DEG C. in the presence of an alkaline catalyst.  Relative quantities of all reactants used vary within wide limits.  In examples cane sugar is reacted with triethylene glycol, formaldehyde, phenol, tertiary butyl phenol and diethylene glycol in the presence of borofluoric acid and perchloric acid, water is removed and the products are reacted with propylene oxide, styrene oxide, allyoxy-2, 3-epoxypropane and butene-1-oxide. The production of resins from the preferred products which have a hydroxyl content of at least 1% by weight, or a hydroxyl number of 150 to 750, is described in Division C3. Lists of starting materials are given including some compounds containing elements other than C, H and O e.g. epichlorhydrin as an alkylene oxide, ethylene cyan- and chlor-hydrin and dichlorhydrin as alcohols, chloral and chloral hydrate as aldehydes and chloro- and nitro-phenols as phenols. Starting hydroxy compounds may also be adducts of alkylene oxides with hydroxy compounds e.g. butan-1, 2-diol, glycerol, cane sugar, hydroquinone and thiodiglycol.  The carbohydrates may be partially acylated or alkylated and sugar anhydrides and acids may be used. Castor oil is an additional specified alcohol. Specification 819,384 is referred to.ALSO:An intermediate suitable for preparing polyurethane resins, is obtained by dissolving a carbohydrate having at least four carbon atoms in a solution of water and an alcohol and/or phenol and an acid catalyst, removing water after reaction of these materials to a residual content of less than one per cent, and reacting the product obtained with a compound containing an alkylene oxide grouping.  Aldehydes and ketones may be condensed with the carbohydrate and alcohol or phenol before the water removal step. In examples cane sugar is reacted with triethylene glycol, formaldehyde, phenol, tertiary butyl phenol and diethylene glycol in the presence of borofluoric acid and perchloric acid; water is removed, and the products are reacted with propylene oxide, styrene oxide, allyoxy-2, 3-epoxy propane and butene -1- oxide; the products thus obtained are then reacted with diphenylmethane-4, 4-diisocyanate, toluylene diisocyanate, thiophosphoric acid tri-o, o-phenylester-4, 41, 411-triisocyanate and an adduct of toluylene diisocyanate and trimethylol propane, in the presence of dibutyl-tin-dilaurate, a polysiloxane - alkylene oxide copolymer, sodium castor oil sulphate, N,N-dimethyl-aminopropylethyl ether, permethylated aminoethyl piperazine, trichloro-monofluoromethane, tin octoate and a polysiloxane-polyalkylene glycol copolymer; some of the polyurethane products are foams.  Lists of starting materials are given. Specification 819,384 is referred to.